This is a terrific idea, thank you.

I would love to hear some of the implications of this approach. I can already think that the attacker would know the size of the file, so that might give him information regarding e.g. the file type. It might be of interest to an attacker to know that most clients get files of a specific size, but a certain client gets a file that is much much larger.

I wonder what other implications might there be.

Great idea, I just need to move my thought of encryption on the sending client to encryption on the destination server since this is infosec related and sending client could be compromised. Thanks for the help!